Category: imidazoles-derivatives

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 31722-49-3, name is 1H-Imidazole-2-carbonitrile, A new synthetic method of this compound is introduced below., SDS of cas: 31722-49-3

Compound 234.2. 5-Iodo-lH-imidazole-2-carbonitrile. Into a 100-mL round- bottom flask, was placed a solution lH-imidazole-2-carbonitrile (compound 234.1, 3.39 g, 36.42 mmol) in sodium hydroxide (54.7 mL, 2 M). Iodine (9.26 g, 36.46 mmol) was added to the reaction. The reaction mixture was stirred for 5h at room temperature. The pH of the solution was adjusted to 5 with HCl (2 M). The aqueous phase was extracted with 3 x 80 mL of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1/1.5) as eluent to furnish 1.02 g (13%) of the title compound as a white solid.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; 3-V BIOSCIENCES, INC.; HEUER, Timothy Sean; OSLOB, Johan D.; MCDOWELL, Robert S.; JOHNSON, Russell; YANG, Hanbiao; EVANCHIK, Marc; ZAHARIA, Cristiana A.; CAI, Haiying; HU, Lily W.; WO2015/95767; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1402838-08-7, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1402838-08-7, name is 2-(1-Trityl-4-imidazolyl)benzaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Different substituted ethan-1-one (1 mol equiv.) was added to asolution of NaOEt (attained from Na (2 mol equiv.) dissolved inEtOH (1.4 M) at 0 C), followed by the addition of intermediate 6(1 mol equiv.). The yellow liquid was stirred at room temperaturefor 3 h. The solvent was removed under reduced pressure and thesaturated NH4Cl solution was added to the mixture to quench thereaction. The mixture was diluted with water, and was extractedwith dichloromethane to afford the crude product, which was usedto the next step without any further purification.

The chemical industry reduces the impact on the environment during synthesis 2-(1-Trityl-4-imidazolyl)benzaldehyde. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zou, Yi; Wang, Fang; Wang, Yan; Sun, Qirui; Hu, Yue; Li, Yuezhen; Liu, Wen; Guo, Wenjie; Huang, Zhangjian; Zhang, Yihua; Xu, Qiang; Lai, Yisheng; European Journal of Medicinal Chemistry; vol. 140; (2017); p. 293 – 304;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 288-32-4,Some common heterocyclic compound, 288-32-4, name is 1H-Imidazole, molecular formula is C3H4N2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

(a) A solution of alpha-bromo-4-tolunitrile (86.6 g) in dichloromethane (1000 mL) is mixed with imidazole (68.0 g). The mixture is stirred at ambient temperature for 15 hours and then diluted with water (1000 mL). Any undissolved solid is removed by filtration and the separated organic solution is then repeatedly washed with water (5*200 mL) to remove excess imidazole, and then dried (MgSO4). The crude product obtained upon evaporation of the solvent can be purified by trituration with cold diethyl ether (200 mL) to obtain 4-(1-imidazolylmethyl)-benzonitrile, m.p. 99-101; HCl salt, m.p. 142-144.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1H-Imidazole, its application will become more common.

Reference:
Patent; Ciba-Geigy Corporation; US4978672; (1990); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 88427-96-7,Some common heterocyclic compound, 88427-96-7, name is 4-(2-Methyl-1H-imidazol-1-yl)benzaldehyde, molecular formula is C11H10N2O, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Working Example 34 4-(6-Chloronaphthanlene-2-sulfonyl)-1-[4-(2-methyl-1H-imidazol-1-yl)benzyl]-2-piperazinone To a solution of N-(tert-butoxycarbonyl)ethylenediamine (431 mg) and 4-(2-methyl-1H-imidazol-1-yl)benzaldehyde (500 mg) in dichloromethane (10 ml) was added acetic acid (323 mg), and the mixture was stirred at room temperature for 1 hour. To the mixture was added, under ice-cooling, sodium triacetoxyborohydride (855 mg), and the mixture was stirred at room temperature for 15 hours. The reaction solution was concentrated, and the residue was dissolved in ethyl acetate. The solution was extracted with water, and the aqueous layer was made alkaline with sodium hydroxide solution. The mixture was extracted with dichloromethane and dried with sodium sulfate, and sodium sulfate was filtered off. To the filtrate was added triethylamine (543 mg) and then was added at 0 C. chloroacetyl chloride (455 mg), and the mixture was stirred at room temperature for 30 minutes. The reaction solution was washed with sodium bicarbonate solution and brine, dried and concentrated, and the residue was dissolved in DMF (15 ml). To the solution was added sodium hydride in oil (129 mg), and the mixture was stirred at room temperature for 3 hours. The reaction solution was concentrated, and the residue was dissolved in ethyl acetate. The solution was washed with water and brine, dried and concentrated, and the residue was purified with column chromatography (ethyl acetate) to give 4-(tert-butoxycarbonyl)-1-[4-(2-methyl-1H-imidazol-1-yl)benzyl]-2-piperazinone.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(2-Methyl-1H-imidazol-1-yl)benzaldehyde, its application will become more common.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US6403595; (2002); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 89830-98-8,Some common heterocyclic compound, 89830-98-8, name is 5-Cyclopropyl-1H-imidazole, molecular formula is C6H8N2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Methyl 5-bromo-2-methylthiophene-3-carboxylate (5.5 g, 23.4 mmol) was added to a 250 mL round bottom flask.4-cyclopropyl-1H-imidazole (2.5 g, 23.4 mmol),Cuprous iodide (669 mg, 3.51 mmol),1,10-phenanthroline (1.3 g, 6.56 mmol),Cesium carbonate (15.2 g, 46.8 mmol) and 100 mL of toluene were reacted at 110 C for 20 hours. When the reaction is over,The reaction solution was concentrated, and the residue was applied to silica gel column chromatographyEthyl acetate = 1: 1) to give the desired product 500mg, yield 8.1%.

The synthetic route of 89830-98-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong Xuanzhu Pharmaceutical Technology Co., Ltd.; Wang Tingzhong; (35 pag.)CN110294746; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 26663-77-4, name is Methyl benzimidazole-5-carboxylate, belongs to imidazoles-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 26663-77-4, category: imidazoles-derivatives

8.2. PREPARATION OF 3,4-DIISOTHIOCYANATOBENZOIC ACID, METHYL ESTER, 11 A 250 ml round bottom flask was charged with 4.98 g (50 mmol) of calcium carbonate, 10 ml of methylene chloride, and 3 ml of water. The resultant slurry was cooled to 10 C. and then 2.27 ml (3.43 g, 30 mmol) of thiophosgene (Aldrich) followed by 2.50 g (14.2 mmol) of 5-benzimidazolecarboxylic acid, methyl ester, 10, dissolved in 50 ml of a 1:1 mixture of acetonitrile in water were slowly added. The reaction mixture was stirred for 4 h and the temperature was allowed to rise to 15-20 C. The orange-white reaction slurry was then filtered and the filtrate was washed with three 50 ml portions of methylene chloride. The organic layers were combined, dried over MgSO4, filtered, and the solvents were removed under vacuum to leave a beige residue. This residue was triturated four times with petroleum ether to leave, after drying for 16 h at 25 C. at 30 mm pressure, 2.14 g (8.56 mmol, 60% yield) of 3,4-diisothiocyanatobenzoic acid, methyl ester, 11, as an off-white powder. 1 H NMR (CDCl3, TMS): delta7.85-7.95 (m, 2H), 7.30 (d, 1H), 3.92 (s, 3H). IR showed a doublet (NCS) at 2140 cm-1.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl benzimidazole-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Cytogen Corporation; US5585468; (1996); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

85692-37-1, name is 1-(1-Methyl-1H-imidazol-2-yl)ethanone, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: 1-(1-Methyl-1H-imidazol-2-yl)ethanone

A mixture of N-(4-ethynylphenyl)-2-(4-formylphenyl)acetamide (184 mg, 0.7 mmol), N-methyl imidazole ketone 2b (99 mg, 0.8 mmol, 1.2 equivalents), piperidine (0.2 ml, 2.1 mmol, 3 equivalents) and anhydrous methanol (5 ml) placed in a 10 mL microwave vial was heated in a microwave synthesizer at 85 C for 6 hours. The crude reaction mixture was concentrated and purified by flash chromatography on silica gel in ethyl acetate/ hexanes (20 %-> 70% ethyl acetate) to obtain 41 (59 mg, 23%). NMR (600 MHz, CDC13) delta 8.09 (d, J = 15.9 Hz, 1H), 7.80 (d, J = 16.0 Hz, 1H), 7.70 (t, J = 6.9 Hz, 2H), 7.39 (s, 4H), 7.35 (d, J = 8.0 Hz, 2H), 7.22 (s, 1H), 7.11 (s, 1H), 7.08 (s, 1H), 4.09 (s, 3H), 3.74 (s, 2H), 3.01 (s, 1H).HRMS calculated 370.1556 found 370.1563 [M+H]+ ion.

The synthetic route of 85692-37-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE UNIVERSITY OF TOLEDO; TILLEKERATNE, Viranga; AL-HAMASHI, Ayad; DLAMINI, Samkeliso; ALQAHTANI, Abdulateef, Saeed; KARAJ, Endri; (69 pag.)WO2019/36607; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 2302-25-2, name is 4-Bromo-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 4-Bromo-1H-imidazole

(Example 177) 2-(4-{2-Fluoro-5-[3-(6-methylpyridin-2-yl)-1H-pyrazol-4-yl]phenyl}-1H-imidazo1-1-yl)ethanol (Compound No. 2-700) (177a) 4-Bromo-1-{2-(trityloxy)ethyl}-1H-imidazole 2-Bromoethanol (1.4 mL, 20 mmol) was dissolved in methylene chloride (50 mL), and triethylamine (3.5 mL, 25 mmol) and trityl chloride (7.0 g, 25 mmol) were added thereto. The resulting mixture was stirred at room temperature for 6 hr. To this reaction solution, water was added. After extraction with ethyl acetate, the organic layer was dried with anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (Yamazen, eluding solvent: hexane/ethyl acetate) to obtain 4.4 g (yield: 60%) of 2-bromoethyl trityl ether as a white solid. N,N-Dimethylformamide (10 mL) was added to a mixture of the resulting 2-bromoethyl trityl ether (1.9 g, 5.1 mmol) and 4-bromoimidazole (0.68 g, 4.6 mmol). The resulting mixture was cooled to 0C, and sodium hydride (60%, oil, 0.22g, 5.5 mmol) was added thereto. The mixture was warmed to room temperature and then stirred for 6 hr. To this reaction solution, water was added. After extraction with ethyl acetate, the organic layer was dried with anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (Yamazen, eluting solvent: hexane/ethyl acetate) to obtain 1.4 g (yield: 69%) of the title compound as a white solid. 1H-NMR (400 MHz, CDCl3) delta ppm: 7.45 (1H, s), 7.29-7.22 (15H, m), 6.89 (1H, s), 4.00 (2H, t, J = 4.9 Hz), 3.36 (2H, t, J = 4.9 Hz).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 2302-25-2.

Reference:
Patent; Sankyo Company, Limited; EP1798229; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 45676-04-8, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 45676-04-8 as follows.

To a 250 mL three-necked flask, 6.8 g of N-tert-butylimidazole and 9.3 g (molar ratio 1: 1) of chloroform were added to a reactor equipped with a magnetic stirrer, a heating apparatus and a condensing apparatus, and toluene was added as a solvent , 2.5 g of sodium hydride as the catalyst, at 90 C, stirring reaction 12h, separation and purification of N-tert-butyl imidazole. 6.2 g of the above product and 6.2 g (molar ratio 1: 1) of chloromethyltrimethylsilane were added to a reaction vessel equipped with a magnetic stirrer, a heating apparatus and a condensing apparatus, 100 mL of toluene as a solvent, argon gas, 120 C for 24 h, and purified to obtain N-methylsilyl (trimethyl) imidazole type ionic liquid.

According to the analysis of related databases, 45676-04-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hangzhou Normal University; Bai, Ying; Peng, Jiajian; Yang, Xioaling; Zhang, Fengxiang; Li, Jiayun; Xiao, Wenjun; (8 pag.)CN106380487; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 4856-97-7, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 4856-97-7, name is (1H-Benzoimidazol-2-yl)methanol belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

1H-benzimidazolyl methanol (2 g, 13.5 mmol) and sodium hydroxide (0.8 g, 20.3 mmol) were dissolved in 20 ml of water.Potassium permanganate (63.9 g, 41 mmol) was added under cooling and stirred at 80 C overnight.After the reaction is completed, the mixture is filtered, and the pH of the filtrate is adjusted to about 3 to precipitate a brown solid.The product was dried to about 1.76. Yield: 78%.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, (1H-Benzoimidazol-2-yl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; China Pharmaceutical University; Wang Jinxin; Shang Yanguo; Song Meng; (13 pag.)CN110156708; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem